Project 365: Day 105 — How to identify an exceptional boss in a sea of mediocrity

Sanika Tillway
100 Naked Words
Published in
4 min readSep 9, 2016

I’ve written enough about the importance of having good mentors or even the freedom that the lack of them allows. In my previous two jobs, I was lucky enough to have bosses that quit within a few months of my joining the organisation (yes, you read that right). In both cases, I hated the fact that my respective bosses had walked out just when I had started to get comfortable with their working styles.

But I now recognize (and it took me a while getting there), that I have grown tremendously because of their absence. I learned to make my own decisions and learn from making my own mistakes. The thing with people who manage (well, most people) is that they’re also (knowingly or unknowingly) prone to micro-managing as per their expectations and I would do that too because I now know the kind of output I expect when I delegate tasks.

But even in my brief stints with my former bosses, or my ongoing stint with my current boss, I have learned that good leadership (even the auto-pilot kind is key to a truly happy team that wants to stick around and do good work. I know a lot of people out there are high performers individually and also in teams, but I firmly believe that one’s performance is a reflection of how good or bad one’s bosses are. Exactly two months into my new job, I sense a quiet reassurance that this is a good job for me, even though it’s a fledgling startup with a few decent clients in its kitty, largely because, my boss who drives it is a good person — professionally and personally. It’s important to remember that work is mostly an assembly line churning out units of job after job after job. But interaction with your core team, your bosses, peers and juniors is what takes up the most amount of your professional time.

I’m in the habit of observing interpersonal interactions in a professional environment even though I largely prefer keeping to myself most of the time. How one interacts with one’s colleagues, one’s mannerisms, body language, temperament — with seniors, juniors and peers is telling of how good one is at managing people. Here are a few points that I use as a compass to identify a terrific boss from the mediocre ones.

Disclaimer: I’ve chosen to focus on the positives of terrific bosses rather than the negatives of bad bosses. Too much has been said about the latter already.

They encourage you to jump off a cliff but also back you if you screw up

The best bosses encourage you to take risks, explore uncharted terrain and really work on projects you haven’t worked on before. They’ll be there to nudge you when you’re being lazy, pressure you into delivering, but if you screw up, they will still have your back. They will tell you shrug off a loss, learn from it so you don’t repeat a mistake, but will also encourage you to move forward.

They encourage you to have a life outside of work

It’s important to have a hustle that is independent of the work one pursues. Though not all side projects are successful or have any quantifiable meaning, a hustle is good fuel for your brain. A good boss always has some consideration for life beyond work, even the most workaholic type does. It’s important to have that to have balance between work and play. By all means, the same boss will push you to put your nose to the grindstone to deliver a job within a tight deadline. But he / she will also tell you to go home and chill after a long day.

They’re organised

Their work-space might be messy but they’re extremely clear about what they want in their heads. Even in their work, their working style has a method, a structure to it. They don’t mess around with big words and promises. They dislike jargon and cut to the chase straightaway. While drawing up a Plan of Action, they preempt potential problems and thus save time.

They take risks

Biggest payoffs of taking risks are for the members of the team, not so much for the boss himself. In taking a good risk, the boss demonstrates courage and conviction in every member of his / her team. If it fails, there’s something to learn. If it results in success, they’ve walked their talk. Which brings me to…

They take one for the team

They let the team take credit for a win. It takes a serious degree of cool and levelheadedness to not get carried away by victories and to give teams credit. Credit is the biggest motivator, bigger even than monetary benefits like appraisals. In their minds, they know that earned respect from one’s team is more powerful than praise heaped by one’s seniors. Ultimately, when push comes to shove, a team supports its leader, who has stood by their side all the time; the leader’s superiors might not.

Humility

No amount of success takes away their humility. It’s hard to find these kind of people. Even some of the best bosses lack this, because success is a wonderful heady cocktail. Humility comes from being grounded and it can’t be taught, it’s usually there for all to see. Which isn’t to say that these people aren’t assertive; they simply acknowledge their achievements quietly than make a show of it and move on to the next milestone than harp about it for months on end.

Authenticity

This is linked to having your team’s back. Honesty in one’s interactions, one’s commitments in a professional environment paves the way for authentic relationships and trust. When your boss can count on you, as a member of his team, you’re among the privileged trusted few. This can only happen through authenticity and confidence and trust — your boss trusts you to deliver which gives you the necessary fuel to not just deliver but also to outperform.

Consistent out-performers, aside from being self-motivated and hungry also have good bosses backing them.

Remember, behind every successful professional, is a boss with a larger vision of success for all stakeholders.

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Sanika Tillway
100 Naked Words

Marketing Consultant. Counselling Psychologist. Human. Become a Medium member to support me & other content creators — with my referral link: bit.ly/3A52jqx